A kind of ligand compound based on bipyridine and its preparation method and application

A ligand compound and bipyridine technology, applied in the field of pharmaceutical compounds, can solve the problems of poor light absorption performance and low photodynamic therapy activity, achieve good absorption capacity, improve photodynamic therapy activity, and strong growth inhibition ability

Active Publication Date: 2021-08-24
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the selection of ligands with poor light absorption ability such as 2-phenylpyridine in traditional iridium complexes, the light absorption performance is poor, and the photodynamic therapy activity is not high.

Method used

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  • A kind of ligand compound based on bipyridine and its preparation method and application
  • A kind of ligand compound based on bipyridine and its preparation method and application
  • A kind of ligand compound based on bipyridine and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The synthesis of bpyCN compound, its structural formula is:

[0039]

[0040] The synthesis method of bpyCN is as follows:

[0041] Mixture of 2,2'-bipyridine-4,4'-dicarbaldehyde (0.106g, 0.5mmol) and 1,2,3,3-tetramethyl-3H-indolium iodide (0.301g, 1mmol) Heated to 80°C in pyridine / ethanol (16mL; 1:15v / v), reacted in the dark under an argon atmosphere for 19 hours, then cooled the reaction to room temperature, filtered and washed the precipitate with ether, and filtered the obtained crude product through ethanol Red-brown crystals were obtained by recrystallization, and the obtained crystals were further dried to obtain 0.241 g of red-brown powder with a yield of 62%. Characterized by NMR, its molecular formula is C 36 h 36 I 2 N 4 , 1 H NMR (500MHz, DMSO-d 6 )δ9.07(d, J=1.7Hz, 2H), 9.00(d, J=5.1Hz, 2H), 8.57(d, J=16.6Hz, 2H), 8.33(dd, J=5.1, 1.7Hz, 2H), 8.07–7.98(m,4H), 7.97–7.93(m,2H), 7.75–7.66(m,4H), 4.29(s,6H), 1.86(s,12H).

Embodiment 2

[0043] The synthesis of bpySN compound, its structural formula is:

[0044]

[0045] The preparation method of bpySN is as follows:

[0046] A mixture of 2,2'-bipyridyl-4,4'-dicarbaldehyde (0.106g, 0.5mmol) and 3-ethyl-2-methylbenzothiazolium iodide (0.305g, 1mmol) in pyridine / ethanol (16mL; 1:15v / v) was heated to 80°C, reacted in the dark under an argon atmosphere for 19 hours, and then the reaction was lowered to room temperature. The precipitate was filtered and washed with ether, and the obtained crude product was recrystallized from ethanol to obtain orange Yellow crystals, and the obtained crystals were further dried to obtain 0.224 g of orange powder, with a yield of 57%. Characterized by NMR, its molecular formula is C 32 h 28 I 2 N 4 S 2 , 1 H NMR (400MHz, DMSO-d 6 )δ8.99–8.96(m,2H),8.55(d,J=8.1Hz,2H),8.43–8.40(m,4H),8.20(dd,J=5.2,1.7Hz,2H),7.99–7.85 (m, 4H), 5.09 (q, J = 7.1 Hz, 4H), 1.53 (t, J = 7.2 Hz, 6H).

Embodiment 3

[0048] The synthesis of bpyPCN compound, its structural formula is:

[0049]

[0050] The preparation method of bpyPCN is as follows:

[0051] A mixture of 2,2'-bipyridyl-4,4'-dicarbaldehyde (0.106g, 0.5mmol) and 1-ethyl iodide 2,3,3-trimethylbenzindole (0.365g, 1mmol) Heated to 80°C in pyridine / ethanol (16mL; 1:15v / v), reacted in the dark under an argon atmosphere for 19 hours, then cooled the reaction to room temperature, filtered and washed the precipitate with ether, and filtered the obtained crude product through ethanol Red-brown crystals were obtained by recrystallization, and the obtained crystals were further dried to obtain 0.294 g of red-brown powder, with a yield of 65%. Characterized by NMR, its molecular formula is C 46 h 44 I 2 N 4 , 1 H NMR (500MHz, DMSO-d 6 )δ9.11(d, J=1.6Hz, 2H), 9.03(d, J=5.1Hz, 2H), 8.71(d, J=16.5Hz, 2H), 8.51(d, J=8.4Hz, 2H) ,8.42–8.35(m,4H),8.30–8.22(m,4H),8.07(d,J=16.6Hz,2H),7.87(ddd,J=8.3,6.8,1.4Hz,2H),7.80(t , J=7.6Hz, 2H), 5...

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Abstract

The present invention relates to the field of pharmaceutical compounds, in particular to a bipyridine-based ligand compound and its preparation method and application. The novel ligand compound obtained on the basis of bipyridine in the present invention has better absorption capacity in the visible light region. It is conducive to the synthesis of complexes with a wider absorption range, improves the activity of photodynamic therapy, and has an inhibitory effect on the growth of cancer cells, especially for human cervical cancer (HeLa cells), which is superior to common bipyridine ligands , contribute to the development of highly effective anticancer drugs.

Description

technical field [0001] The invention relates to the field of medical compounds, in particular to a bipyridyl-based ligand compound and its preparation method and application. [0002] technical background [0003] Since the twentieth century, cancer has become one of the major hazards plaguing human health. About 8.8 million people die of cancer every year in the world, accounting for nearly one-sixth of the total death toll. Every year, 14 million cancer patients are diagnosed worldwide. In my country, about 2.2 million people die of cancer every year, and the trend is gradually increasing every year. Cancer treatment mainly includes three aspects: surgery, radiation therapy and chemotherapy. Chemotherapy is the method of treating diseases with chemically synthesized drugs. Chemotherapy is currently one of the main means of treating tumors and some autoimmune diseases. Chemotherapy refers to the application of drugs to treat cancer. These special drugs can kill tumor cells...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D417/14A61P35/00
CPCA61P35/00C07D401/14C07D417/14
Inventor 黄怀义祝梓琳缪梦昭范中贤
Owner SUN YAT SEN UNIV
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